N-alkoxy-n-phenylcarbamate derivatives

ABSTRACT

Compounds of formula (I) wherein R 1  is C 1 -C 4 -alkyl or cyclopropyl; R 2  is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl; or C 1 -C 6 -alkyl substituted by 1 to 5 fluorine atoms; R 3  is C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkinyl, C 2 -C 6 -alkinyloxy, C 1 -C 6 -alkoxycarbonyl, CN, or aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by identical of different substituents, R 5  signifies hydrogen or methyl; R 6  and R 7  are C 1 -C 4 -alkyl; have microbicidal, insecticidal and acaricidal activity and may be used for the control of pests and plant-pathogenic fungi in agriculture, horticulture and in the field of hygiene.

FIELD OF THE INVENTION

The present invention relates to new N-alkoxy-N-phenylcarbamates having microbicidal, insecticidal and acaricidal activity, a process for their preparation, new intermediates for the preparation thereof, agrochemical compositions containing these active ingredients, as well as the use thereof in the control and prevention of plant-pathogenic fungi, acarids and insects in agriculture and in the field of hygiene.

DETAILED DESCRIPTION

The new N-alkoxy-N-phenylcarbamates fall within formula I,

wherein:

R₁ is C₁-C₄-alkyl or cyclopropyl;

R₂ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl; or C₁-C₆-alkyl substituted by 1 to 5 fluorine atoms;

R₃ is C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₂-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl or CN, whereby, with the exception of CN, the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, aminocarbonyl, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, whereby the cyclic radicals in turn may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, optionally substituted benzyl, optionally substituted benzyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl and optionally substituted heteroaryloxy; whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or

R₃ signifies aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halogen-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-(C₁-C₆-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, C₁-C₆-alkylaminothiocarbonyl, di-(C₁-C₆-alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)-amino, NO₂, an unsubstituted C₁-C₄-alkylenedioxy group or one which is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen; or CN, SF₅, OH and QR₄;

Q signifies a direct bond, O, O(C₁-C₆-alkylene), (C₁-C₆-alkylene)O, S(═O)p, S(═O)p(C₁-C₆-alkylene), (C₁-C₆-alkylene)S(═O)p, C₁-C₈-alkylene, C₂-C₆-alkenylene or C₂-C₆-alkinylene;

R₄ signifies an unsubstituted C₂-C₆-alkenyl- or C₂-C₆-alkinyl group or one which is substituted by 1 to 3 halogen atoms, a (C₁-C₄-alkyl)₃Si group, whereby the alkyl groups may be identical or different, CN, an unsubstituted or mono- to penta-substituted C₃-C₆-cycloalkyl, aryl, heteroaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, phenoxy, CN, SF₅, NO₂, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halogen-C₁-C₆-alkylsulfonyl and C₁-C₄-alkylenedioxy, the latter being unsubstituted or mono- to tetrasubstituted by C₁-C₄-alkyl and/or by halogen;

p is 0, 1 or 2;

R₅ signifies hydrogen or methyl;

R₆ and R₇ are C₁-C₄-alkyl;

According to the present application, formula I includes all isomeric forms and mixtures thereof, e.g. racemic mixtures and any [E/Z] mixtures. Alkyl—as a group per se and as a structural element of other groups and compounds, such as of halogenalkyl, alkoxy and alkylthio—is either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl.

Alkenyl—as a group per se and as a structural element of other groups and compounds, such as of halogenalkenyl—is either straight-chained, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, e.g. isopropenyl.

Alkinyl—as a group per se and as a structural element of other groups and compounds, such as of halogenalkinyl—is either straight-chained, e.g. propargyl, 2-butinyl or 5-hexinyl, or branched, e.g. 2-ethinylpropyl or 2-propargylisopropyl.

Alkylenedioxy is —O(alkylene)O—.

Alkylene is either straight-chained, e.g. —CH₂CH₂—, —CH₂CH₂CH₂— or —CH₂CH₂CH₂CH₂—, or branched, e.g. —CH(CH₃)—, —CH(C₂H₅)—, —C(CH₃)₂—, —CH(CH₃)CH₂— or —CH(CH₃)CH(CH₃)—.

Alkenylene is either straight-chained, e.g. vin-1,2-ylene, all-1,3-ylene, but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, e.g. 1-methylvin-1,2-ylene.

Alkinylene is either straight-chained, e.g. propargylene, 2-butinylene or 5-hexinylene, or branched, e.g. 2-ethinylpropylene or 2-propargylisopropylene.

Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Halogenalkyl may contain identical or different halogen atoms.

Aryl signifies phenyl or naphthyl, preferably phenyl.

Heteroaryl signifies a cyclic aromatic group with 5 to 9 ring members in one or two rings, of which 1 to 3 members are hetero atoms selected from the group oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed on the heterocycle, the binding to the residual molecule taking place either through the hetero or the benzene moiety.

Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl, imidazolyl, indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, pudnyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo[3,4-b]pyridyl, pyridyl, pyrimidinyl, pyrrolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl and triazolyl.

Preference is given to pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl.

Heterocyclyl signifies a 5- to 7-membered, non-aromatic ring with one to three hetero atoms selected from the group comprising N, O and S. Preference is given to non-aromatic 5- and 6-rings that have one nitrogen atom as a hetero atom and optionally one further hetero atom.

Preference is given to pyrazolinyl, thiazolinyl and oxazolinyl.

Of the compounds of formula I, those groups are preferred, wherein:

(1)

a) R₁ is methyl, ethyl or cyclopropyl, preferably methyl; or

b) R₂ is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl; or

c) R₃ is C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy or C₁-C₆-alkoxycarbonyl, whereby the above-mentioned groups may be partially or wholly halogenated; furthermore CN, OCN or halogen; or

d) R₃ signifies phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkythio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or

e) R₃ signifies phenyl which is substituted, preferably in 4-position, by QR₄, wherein Q is a direct bond, O, OCH₂, CH₂O, S, CH₂—CH₂, —CH═CH— or —C≡C— and R₄ signifies phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, C₂-C₄-alkinyl, C₃-C₄-alkinyloxy, C₁-C₄-alkoxycarbonyl or CN; or

f) R₃ signifies pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl; or

g) R₅ signifies hydrogen, or

h) R₆ and R₇ signify methyl or ethyl, preferably methyl.

(2) Compounds of formula I, wherein:

R₁ is methyl or ethyl, preferably methyl;

R₂ signifies methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl;

R₃ signifies C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy or C₁-C₆-alkoxycarbonyl, whereby the above-mentioned groups may be partly or wholly halogenated; furthermore CN, OCN or halogen; or

phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl; and

R₆ and R₇ signify methyl or ethyl, preferably methyl.

(2a) Of those mentioned under (2), especially those in which:

R₃ signifies phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl.

(3) Compounds of formula I, wherein:

R₁ is methyl or ethyl, preferably methyl;

R₂ is C₁-C₆-alkyl or C₁-C₆-alkyl substituted by 1 to -5 fluorine atoms;

R₃ is C₁-C₆alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, CN, C₃-C₆-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby, with the exception of CN, the above-mentioned groups may be substituted as mentioned above;

R₆ and R₇ are methyl or ethyl, preferably methyl.

(3a) Of those mentioned under (3), especially those in which:

R₂ is C₁-C₆-alkyl, fluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl;

R₃ is C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, CN, C₃-C₆-cycloalkyl, phenyl which is unsubstituted or mono- to tni-substituted by identical or different substituents from halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, CN, OCN, benzyl, phenyl, or phenyloxy, wherein these aromatic groups are unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl or C₁-C₂-alkoxy.

(3b) Of those mentioned under (3a), especially those in which:

R₃ is C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl, or phenyl which is unsubstituted or mono- to disubstituted by halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl or C₁-C₂-alkoxy.

(4) Compounds of formula I, wherein:

R₁ is methyl, ethyl or cyclopropyl, preferably methyl;

R₂ is C₁-C₆-alkyl, preferably methyl or ethyl;

R₃ is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₁-C₆-alkoxycarbonyl, CN, C₃-C₆-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the hydrocarbon radicals and the cyclic radicals may be substituted as mentioned above;

(4a) Of those mentioned under (4), especially those in which:

R₃ is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl.

(4b) Of those mentioned under (4), especially those in which:

R₃ is phenyl which is unsubstituted or mono- or disubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, benzyl, phenyl, or phenyloxy, wherein these aromatic groups are unsubstituted or mono- or disubstituted by halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl or C₁-C₂-alkoxy.

(5) Compounds of formula I, wherein:

R₁ signifies methyl, ethyl or cyclopropyl;

R₂ signifies C₁-C₆-alkyl, preferably methyl or ethyl, C₂-C₆-alkenyl, preferably allyl or C₂-C₆-alkinyl, preferably propargyl.

R₃ signifies phenyl which may be substituted by one or more identical or different substituents selected from the group comprising halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkyl-sulfonyl, halogen-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-(C₁-C₆-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, C₁-C₆-alkylaminothiocarbonyl, di-(C₁-C₆-alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)-amino, NO₂, an unsubstituted C₁-C₄-alkylenedioxy group or one which is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen; or CN, SF₅, OH and QR₄;

Q signifies a direct bond, O, O(C₁-C₆-alkylene), (C₁-C₆-alkylene)O, C₁-C₈-alkylene, C₂-C₆-alkenylene or C₂-C₆-alkinylene;

R₄ signifies an unsubstituted or mono- to penta-substituted C₃-C₆-cycloalkyl, aryl, heteroaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, phenoxy, CN, SF₅, NO₂, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halogen-C₁-C₆-alkylsulfonyl and an unsubstituted C₁-C₄-alkylenedioxy or one that is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen.

(5a) Of those mentioned under (5), especially those in which:

R₃ signifies phenyl which is substituted, preferably in 4-position, by QR₄, wherein Q is a direct bond, O, OCH₂, CH₂O, S, CH₂—CH₂, —CH═CH— or —C≡C— and

R₄ signifies phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, C₂-C₄-alkinyl, C₃-C₄-alkinyloxy, C₁-C₄-alkoxycarbonyl or CN.

Compounds of formula I may be produced as follows:

A) A compound of formula I is produced whereby a hydrazone of the general formula II

wherein R₁, R₂ and R₃ have the significances given for formula I, is reacted with an aldehyde or a ketone of the general formula III or with one of its acetal or imino derivatives of the general formulae IVa and IVb

wherein R₈ signifies optionally substituted C₁-C₆-alkyl or the two R₈, together with the two oxygen atoms and the carbon to which they are bonded, signify a cyclic acetal.

The compounds of the general formulae II and III are known from literature (e.g. Ablov et al., Russ.J.Inorg.Chem. (Engl.Transl.), 11, 1966, 39,40; Barton, Derek H. R.; Bashiardes, George; Fourrey, Jan-Louis, Tetrahedron, 44, 1, 1988, 147-162; WO 93/15046) or may be produced by methods known per se. The compounds of the general formulae IVa and IVb may be obtained analogously to the methods described under B) and C) or directly from the carbonyl derivatives of formula III.

B) A compound of formula I is produced whereby a N-hydroxycarbamate of the general formula V,

wherein R₁—R₃, R₅ and R₆ are defined as for formula I, is etherified. The compounds of the general formula V are novel and may be produced whereby

a) a N-hydroxyaniline of the general formula VI

wherein R₁—R₃ and R₅ have the significances given for formula I, is reacted with a chloroformic acid ester of the general formula VII

Cl—COOR₆  VII

 or

b) a carbonyl compound of the general formula VIII

wherein R₅ and R₆ have the significances given for formula I, or one of its acetal or imino derivatives VIIIa or VIIIb, is condensed with a hydrazone of the general formula II.

The compounds of formula VI are novel and may be produced by one of the following methods:

aa) a hydrazone of the general formula II is condensed with an aldehyde or ketone of the general formula IX or with one of its acetal or imino derivatives IXa or IXb

wherein R₅ is defined as for formula I and R₈ is defined as for formula IV. The compounds of formula IX are known (e.g. Bamberger, Elger; Chem. Ber. 36, 3653 (1903); Fijalek, Z.; Zuman, P.; Electroanalysis 5, 53 (1993); Barth, A.; et al.; J.Am. Chem Soc. 119, 4149 (1997); Karakus C.; Zuman, P.; J.Electronanal. Chem. 396, 499 (1995)) and the acetal and imino derivatives thereof may be produced by methods known per se.

ab) a hydrazone of the general formula X

wherein R₅ signifies hydrogen or methyl, is condensed with a ketone of formula XI

wherein R₁ to R₃ are as defined under formula I.

The compounds of formulae X and XI are known (e.g. Buhlmann; Einhorn; Chem. Ber. 34, 3791 (1901)) or may be produced by methods known per se.

ac) A nitro compound of the general formula XII

wherein R₁—R₃ and R₅ are as defined under formula I, is reduced analogously to the methods indicated for the preparation of compounds of formula IX. The compounds of formula XII are novel and may be obtained e.g. by condensation of the corresponding nitrocarbonyl derivatives with hydrazones of formula II.

The compounds of formula VIII are novel and may be prepared by reacting a hydroxyaniline of formula IX with a chloroformic acid ester of formula VII.

C) A compound of formula I is produced whereby an alkoxyaniline of the general formula XIII

wherein R₁—R₃, R₅ and R₇ are defined as for formula I, is reacted with a chloroformic acid ester of the general formula VII.

The compounds of formula XIII are novel and may be produced by one of the following methods:

a) A hydrazone of formula II is condensed with an aldehyde or ketone of the general formula XIV or with one of its acetal or imino derivatives

wherein R₅ and R₇ are defined as for formula I and R₈ is defined as for formula IV.

The compounds of formulae XIV, XVa and XVb are novel and may be prepared by etherification of the N-hydroxy derivatives of formula IX.

b) A ketone of formula XI is condensed with a hydrazone of the general formula XVI

wherein R₅ and R₇ are as defined under formula I. The compounds of formulae XVI are novel and may be prepared by etherificafion of the N-hydroxy derivatives of formula X.

D) A compound of formula I is produced whereby an oxime of the general formula XVII

wherein R₁, R₃, and R₅ to R₇ are defined as for formula I, is etherified.

The compounds of formula XVII are novel and may be obtained whereby

a) a ketone of the general formula XVIII

wherein R₁, R₃ and R₅—R₇ have the significances given for formula I, is reacted with hydroxylamine or with one of its salts, or

b) a compound of the general formula XIX,

wherein R₁, R₃ and R₅—R₇ are defined as for formula I, is reacted with nitrous acid or with an alkyl nitrite in the presence of an acid or base, or

c) a hydrazone of the general formula XX

wherein R₁ and R₃ are defined as for formula I, is reacted with an aldehyde or ketone of the general formula III or with an acetal or imine of the general formulae IVa or IVb, as a described under A).

The compounds of formulae XVIII and XIX are novel and may be obtained analogously to the preparation of the compounds of formula I.

The compounds of formula XX are known (e.g. Barany et al., J.Chem.Soc., 1951, 1929; Neber; Hartung; Ruopp, Chem.Ber., 58, 1925, 1240; Gnichtel, Horst; Toepper, Bernhard, Liebigs Ann.Chem., GE, 1989, 1071-1074; Rapoport,H.; Nilsson,W., J.Amer.Chem.Soc., 83, 1961, 4262-4267).

E) A compound of formula I may be produced whereby a ketone of the general formula XVIII is reacted with an alkoxyamine of the general formula XXI

R₂—ONH₂  XXI

wherein R₂ is defined as for formula I, or with one of its salts.

All the above-described reactions are known per se. The novel, above-mentioned intermediates were developed especially for the present invention and similarly form an object of this invention. Those of formulae IV, V, VI, VIII, XII-XIX are of particular significance.

The compounds of formula I are of preventive and/or curative merit as active ingredients for the control of plant pests and may be used in the agricultural sector and related fields The active ingredients of formula I according to the invention are notable for their good activity even at low concentrations, for their good plant tolerance and for their environmental acceptability. They possess very advantageous, especially systemic properties, and may be used for the protection of numerous cultivated plants. Using the active ingredients of formula I, pests appearing on plants or plant parts (fruits, flowers, foliage, stems, tubers, roots) of different crops can be checked or destroyed, whereby parts of the plant which grow later are also protected e.g. from phytopathogenic micro-organisms.

The compounds of formula I may also be be employed as a dressing for seeds (fruits, tubers, grain) and plant cuttings to protect against fungal infections, and to protect against phytopathogenic fungi appearing in the soil.

Compounds I are effective for example against the phytopathogenic fungi belonging to the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e.g. Phytophthora, Pythium, Plasmopara).

Target cultivations for the plant-protecting usage in the context of the invention are, for example, the following species of plant: cereals, (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybean); oleaginous fruits (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (squashes, cucumbers, melons); fibrous plants (cotton, flax, hemp or jute); citrus fruits (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); Lauraceae (avocado, cinnamon, camphor); and plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, banana plants, natural rubber plants and ornamental.

In addition, the compounds of formula I according to the invention are valuable active ingredients against insects and pests of the order Acarina, such as those appearing on crop plants and ornamentals in agriculture and horticulture and in forestry, whilst being tolerated well by warm-blooded animals, fish and plants. The compounds of formula I are especially suitable for controlling pests in cultivations of cotton, vegetables, fruit and rice, such as spider mites, aphids, caterpillars and plant and leaf hoppers in rice. The pests which are primarily controlled are spider mites such as Panonychus ulmi, aphids such as Aphis craccivora, caterpillars such as those of Heliothis virescens and plant and leaf hoppers in rice, such as Nilaparvata lugens or Nephotettix cincticeps.

The good pesticidal activity of the compounds I according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned.

Further fields of application for the active ingredients according to the invention are the protection of stock and material, where the goods stored are protected against rotting and mildew, as well as against animal pests (e.g. grain weevils, mites, maggots, etc). In the hygiene sector, compounds of formula I provide successful control of animal parasites such as ticks, mites, warble flies etc., on domestic animals and productive livestock Compounds I are effective against individual or all stages of development of pests showing normal sensitivity, and also of those showing resistance Their activity may be demonstrated, for example, by the mortality of the pests, which occurs immediately or only after some time, for example during a moult, or by reduced egg laying and/or hatching rate.

Compounds I are used in this instance in unmodified form or preferably together with the excipients that are usual in formulation technology. To this end, they are suitably processed in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts or granules, e.g. by encapsulation in e.g. polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.

Suitable carriers and additives may be solid or liquid and are substances that are appropriate in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilisers.

The compounds of formula I may be mixed with further active ingredients, e.g. fertilisers, trace element intermediates or other plant-protecting compositions, especially with further fungicides. Unexpected synergistic effects may thus occur.

Preferred mixture components are:

azoles, such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, tritconazole; pynmidinyl carbinols, such as ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such as bupinmate, dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil; pyrroles, such as fenpiclonil, fludioxonil; phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozolin; carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine;

strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, CGA 279202 (trifloxystrobin); dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; N-halogenmethylthiophthalimides, such as captafol, captan, dichlofluanid, fluoromide, folpet, tolyfluanid; Cu compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper; nitrophenol derivatives, such as dinocap, nitrothal-isopropyl; organo-P derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen,. pyrazophos, tolclofos-methyl; various, such as AC 382042, acibenzolar-S-methyl, anilazine, blasticidin-S, quinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fenhexamid, fentin, ferimzone, fluazinam, flusulfamide, fosetyl-aluminium, hymexazol, IKF-916, iprovalicarb, kasugamycin, methasulfocarb, MON65500, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, RH-7281, RPA 407213, sulfur, triazoxide, tricyclazole, triforine, validamycin.

One preferred method of applying an active ingredient of formula I or an agrochemical composition containing at least one of these active ingredients is application to the foliage (leaf application). The frequency and rate of application depend on the severity of infestation by the invader in question. However, the active ingredients I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plants with a liquid preparation, or by applying the substances to the soil in solid form, for example in granular form (soil application). With paddy rice cultures, granules may be metered into the flooded paddy field. The compounds I may also be applied to seed grain for seed pre-treatment (coating) by either drenching the grains or tubers in a liquid preparation of the active ingredient or coating them with a solid preparation. The compositions are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredient with extenders, such as solvents, solid carriers and optionally surface-active compounds (surfactants).

The agrochemical compositions normally contain 0.1 to 99 percent by weight, especially 0.1 to 95 percent by weight, of active ingredient of formula 1, 99.9 to 1 percent by weight, especially 99.8 to 5 percent by weight, of a solid or liquid additive and 0 to 25 percent by weight, especially 0.1 to 25 percent by weight, of a surfactant.

Favourable application rates generally lie between 1 g and 2 kg of active substance (AS) per hectare (ha), preferably between 10 g and 1 kg AS/ha, especially between 20 g and 600 g AS/ha.

For usage as a seed dressing, the dosages advantageously used are 10 mg to 1 g of active substance per kg seeds.

Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

The compositions may also contain further additives, such as stabilisers, anti4oaming agents, viscosity regulators, binding agents or tackifiers, as well as fertilisers or other active ingredients, in order to achieve special effects.

Preparation Example P-1) N-(2-formylphenyl)N-methoxycarbamic acid methyl ester

A solution of 27.4 g of (2-bromomethyl-phenyl)-N-methoxycarbamic acid methyl ester in 50 ml of acetonitrile is added dropwise at room temperature to 40 g of N-methyl-morpholine-N-oxide in 150 ml of acetonitrile. After stirring for 16 hours, the mixture is concentrated and the residue partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate and, after drying over sodium sulphate, the solvent is distilled from the combined organic phases. The residue is purified on silica gel using ethyl acetate/hexane (1:5% by volume). The title compound is obtained in the form of a yellow oil.

H-2) N-methoxy-{2-[(2-methoxyimino-1-methyl-2-(4-fluorophenyl)-ethylidene)-hydrazonomethyl]-phenyl}-carbamic acid methyl ester

A solution of 1.05 g of (2-formyl-phenyl)-N-methoxycarbamic acid methyl ester and 1.05 g of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime in 5 ml of methanol is stirred at room temperature for 4 hours. The resulting by-product (symmetric azine of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime) is removed by filtration and the filtrate is placed in a refrigerator over night. The product which has crystallised is filtered off (1.0 g). By concentrating the mother liquor and by means of fractional crystallisation of the residue, a further 0.48 g of the title compound are obtained in the form of yellow crystals having a melting point of 88-90° C.

The compounds of the following tables may be produced in analogous manner. Abbreviations: i: iso; s: sec; t: tert

Table 1

Compounds of the general formula I.1, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 2

Compounds of the general formula I.1, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 3

Compounds of the general formula I.1, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 4

Compounds of the general formula I.1, in which R₂ signifies 2,2,2-trifluoroethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 5

Compounds of the general formula I.1, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 6

Compounds of the general formula I.1, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 7

Compounds of the general formula I.1, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 8

Compounds of the general formula I.1, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 9

Compounds of the general formula I.1, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 10

Compounds of the general formula I.1, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 11

Compounds of the general formula I.2, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 12

Compounds of the general formula I.2, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 13

Compounds of the general formula I.2, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 14

Compounds of the general formula I.2, in which R₂ signifies 2,2,2-trifluoroethyl and R₈ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 15

Compounds of the general formula I.2, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 16

Compounds of the general formula I.2, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 17

Compounds of the general formula I.2, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 18

Compounds of the general formula I.2, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 19

Compounds of the general formula I.2, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 20

Compounds of the general formula I.2, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 21

Compounds of the general formula I.3, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 22

Compounds of the general formula I.3, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 23

Compounds of the general formula I.3, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 24

Compounds of the general formula I.3, in which R₂ signifies 2,2,2-trifluoroethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 25

Compounds of the general formula I.3, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 26

Compounds of the general formula I.3, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 27

Compounds of the general formula I.3, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 28

Compounds of the general formula I.3, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 29

Compounds of the general formula I.3, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 30

Compounds of the general formula I.3, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 31

Compounds of the general formula I.4, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 32

Compounds of the general formula I.4, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 33

Compounds of the general formula I.4, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 34

Compounds of the general formula I.4, in which R₂ signifies 2,2,2-trifluoroethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 35

Compounds of the general formula I.4, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 36

Compounds of the general formula I.4, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 37

Compounds of the general formula I.4, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 38

Compounds of the general formula I.4, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 39

Compounds of the general formula I.4, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 40

Compounds of the general formula I.4, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 41

Compounds of the general formula I.5, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 42

Compounds of the general formula I.5, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 43

Compounds of the general formula I.5, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 44

Compounds of the general formula I.5, in which R₂ signifies 2,2,2-trifluoroethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 45

Compounds of the general formula I.5, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 46

Compounds of the general formula I.5, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 47

Compounds of the general formula I.5, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 48

Compounds of the general formula I.5, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 49

Compounds of the general formula I.5, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 50

Compounds of the general formula I.5, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 51

Compounds of the general formula I.6, in which R₂, R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 52

Compounds of the general formula I.6, in which R₂ signifies ethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 53

Compounds of the general formula I.6, in which R₂ signifies difluoromethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 54

Compounds of the general formula I.6, in which R₂ signifies 2,2,2-trifluoroethyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

Table 55

Compounds of the general formula I.6, in which R₂ and R₆ signify methyl and R₇ signifies ethyl and R₃ corresponds in each case to one line of Table A.

Table 56

Compounds of the general formula I.6, in which R₂ and R₇ signify ethyl and R₆ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 57

Compounds of the general formula I.6, in which R₂ and R₆ signify ethyl and R₇ signifies methyl and R₃ corresponds in each case to one line of Table A.

Table 58

Compounds of the general formula I.6, in which R₂ signifies methyl and R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 59

Compounds of the general formula I.6, in which R₂, R₆ and R₇ signify ethyl and R₃ corresponds in each case to one line of Table A.

Table 60

Compounds of the general formula I.6, in which R₂ signifies n-propyl and R₆ and R₇ signify methyl and R₃ corresponds in each case to one line of Table A.

TABLE A No. R₃ 1. CH₃ 2. CH₂CH₃ 3. (CH₂)₂CH₃ 4. (CH₂)₃CH₃ 5. (CH₂)₄CH₃ 6. (CH₂)₅CH₃ 7. CH(CH₃)₂ 8. C(CH₃)₃ 9. CH₂CH(CH₃)₂ 10. CH(CH₃)CH₂CH₃ 11. OCH₃ 12. OCH₂CH₃ 13. O(CH₂)₂CH₃ 14. O(CH₂)₃CH₃ 15. O(CH₂)₄CH₃ 16. OCH(CH₃)₂ 17. OCH(CH₃)CH₂CH₃ 18. OC(CH₃)₃ 19. CH═CH₂ 20. CH═CHCH₃ 21. CH═C(CH₃)₂ 22. CH₂CH═CH₂ 23. CH₂CH═CHCH₃ 24. OCH₂CH═CH₂ 25. C≡CH 26. C≡CCH₃ 27. C≡CC(CH₃)₃ 28. CH₂C≡CH 29. CH₂C≡CCH₃ 30. OCH₂C≡CH₃ 31. OCH₂C≡C—C(CH₃)₃ 32. C(O)OCH₃ 33. C(O)OCH₂CH₃ 34. C(O)O(CH₂)₂CH₃ 35. C(O)O(CH₂)₃CH₃ 36. C(O)O(CH₂)₄CH₃ 37. C(O)OCH(CH₃)₂ 38. C(O)OC(CH₃)₃ 39. CN 40. Cl 41. Br 42. CF₃ 43. CH₂CF₃ 44. CH₂CH₂F 45. CH₂CN 46. CH₂OCH₃ 47. CH₂OCH₂CH₃ 48. (CH₂)₂COOCH₃ 49. (CH₂)₂CONH₂ 50. (CH₂)₂CONHCH₃ 51. (CH₂)₂CON(CH₃)₂ 52. (CH₂)₂SCH₃ 53. CH₂OCH₂CH═CH₂ 54. CH₂-cycl-C₃H₅ 55. CH₂-cycl-C₆H₁₁ 56. CH═CF₂ 57. C≡C—Br 58. C≡C—OCH₃ 59. Cyclopropyl 60. Cyclobutyl 61. Cyclopentyl 62. Cyclohexyl 63. Phenyl 64. 1-Naphthyl 65. 2-Naphthyl 66. 2-F—C₆H₄ 67. 3-F—C₆H₄ 68. 4-F—C₆H₄ 69. 2,3-F₂—C₆H₃ 70. 2,4-F₂—C₆H₃ 71. 2,5-F₂—C₆H₃ 72. 2,6-F₂—C₆H₃ 73. 3,4-F₂—C₆H₃ 74. 3,5-F₂—C₆H₃ 75. 2-Cl—C₆H₄ 76. 3-Cl—C₆H₄ 77. 4-Cl—C₆H₄ 78. 2,3-Cl₂—C₆H₃ 79. 2,4-Cl₂—C₆H₃ 80. 2,5-Cl₂—C₆H₃ 81. 2,6-Cl₂—C₆H₃ 82. 3,4-Cl₂—C₆H₃ 83. 3,5-Cl₂—C₆H₃ 84. 2,3,4-Cl₃—C₆H₂ 85. 2,3,5-Cl₃—C₆H₂ 86. 2,3,6-Cl₃—C₆H₂ 87. 2,4,5-Cl₃—C₆H₂ 88. 2,4,6-Cl₃—C₆H₂ 89. 3,4,5-Cl₃—C₆H₂ 90. 2-Br—C₆H₄ 91. 3-Br—C₆H₄ 92. 4-Br—C₆H₄ 93. 2,3-Br₂—C₆H₃ 94. 2,4-Br₂—C₆H₃ 95. 2,5-Br₂—C₆H₃ 96. 2,6-Br₂—C₆H₃ 97. 3,4-Br₂—C₆H₃ 98. 3,5-Br₂—C₆H₃ 99. 2-F-3-Cl—C₆H₃ 100. 2-F-4-Cl—C₆H₃ 101. 2-F-5-Cl—C₆H₃ 102. 2-F-3-Br—C₆H₃ 103. 2-F-4-Br—C₆H₃ 104. 2-F-5-Br—C₆H₃ 105. 2-Cl-3-Br—C₆H₃ 106. 2-Cl-3-Br—C₆H₃ 107. 2-Cl-5-Br—C₆H₃ 108. 3-F-4-Cl—C₆H₃ 109. 3-F-5-Cl—C₆H₃ 110. 3-F-6-Cl—C₆H₃ 111. 3-F-4-Br—C₆H₃ 112. 3-F-5-Br—C₆H₃ 113. 3-F-6-Br—C₆H₃ 114. 3-Cl-4-Br—C₆H₃ 115. 3-Cl-5-Br—C₆H₃ 116. 3-Cl-6-Br—C₆H₃ 117. 4-F-5-Cl—C₆H₃ 118. 4-F-6-Cl—C₆H₃ 119. 4-F-5-Br—C₆H₃ 120. 4-F-6-Br—C₆H₃ 121. 4-Cl-5-Br—C₆H₃ 122. 5-F-6-Cl—C₆H₃ 123. 5-F-6-Br—C₆H₃ 124. 5-Cl-6-Br—C₆H₃ 125. 3-Br-4-Cl-5-Br—C₆H₂ 126. 2-CN—C₆H₄ 127. 3-CN—C₆H₄ 128. 4-CN—C₆H₄ 129. 3-OCN—C₆H₄ 130. 4-CN—C₆H₄ 131. 2-CH₃O—C₆H₄ 132. 3-CH₃O—C₆H₄ 133. 4-CH₃O—C₆H₄ 134. 2,3-(CH₃O)₂—C₆H₃ 135. 2,4-(CH₃O)₂—C₆H₃ 136. 2,5-(CH₃O)₂—C₆H₃ 137. 3,4-(CH₃O)₂—C₆H₃ 138. 3,5-(CH₃O)₂—C₆H₃ 139. 3,4,5-(CH₃O)₃—C₆H₂ 140. 2-C₂H₅O—C₆H₄ 141. 3-C₂H₅O—C₆H₄ 142. 4-C₂H₅O—C₆H₄ 143. 2-(n-C₃H₇O)—C₆H₄ 144. 3-(n-C₃H₇O)—C₆H₄ 145. 4-(n-C₃H₇O)—C₆H₄ 146. 2-(i-C₃H₇O)—C₆H₄ 147. 3-(i-C₃H₇O)—C₆H₄ 148. 4-(i-C₃H₇O)—C₆H₄ 149. 4-(n-C₄H₉)—C₆H₄ 150. 3-(t-C₄H₉)—C₆H₄ 151. 4-(t-C₄H₉)—C₆H₄ 152. 2-Allyl-O—C₆H₄ 153. 3-Allyl-O—C₆H₄ 154. 4-Allyl-O—C₆H₄ 155. 2-CF₃—C₆H₄ 156. 3-CF₃—C₆H₄ 157. 4-CF₃—C₆H₄ 158. 2-Acetyl-C₆H₄ 159. 3-Acetyl-C₆H₄ 160. 4-Acetyl-C₆H₄ 161. 2-Methoxycarbonyl-C₆H₄ 162. 3-Methoxycarbonyl-C₆H₄ 163. 4-Methoxycarbonyl-C₆H₄ 164. 2-Aminocarbonyl-C₆H₄ 165. 3-Aminocarbonyl-C₆H₄ 166. 4-Aminocarbonyl-C₆H₄ 167. 2-Dimethylaminocarbonyl-C₆H₄ 168. 3-Dimethylaminocarbonyl-C₆H₄ 169. 4-Dimethylaminocarbonyl-C₆H₄ 170. 2-(N-Methylaminocarbonyl)-C₆H₄ 171. 3-(N-Methylaminocarbonyl)-C₆H₄ 172. 4-(N-Methylaminocarbonyl)-C₆H₄ 173. 2-CH₃S—C₆H₄ 174. 3-CH₃S—C₆H₄ 175. 4-CH₃S—C₆H₄ 176. 2-CH₃SO₂—C₆H₄ 177. 3-CH₃SO₂—C₆H₄ 178. 4-CH₃SO₂—C₆H₄ 179. 2-CF₃O—C₆H₄ 180. 3-CF₃O—C₆H₄ 181. 4-CF₃O—C₆H₄ 182. 2-CHF₂O—C₆H₄ 183. 3-CHF₂O—C₆H₄ 184. 4-CHF₂O—C₆H₄ 185. 3-CF₃-4-CF₃O—C₆H₃ 186. 2-CH₃NH—C₆H₄ 187. 3-CH₃NH—C₆H₄ 188. 4-CH₃NH—C₆H₄ 189. 2-(CH₃)₂N—C₆H₄ 190. 3-(CH₃)₂N—C₆H₄ 191. 4-(CH₃)₂N—C₆H₄ 192. 2-Ethoxycarbonyl—C₆H₄ 193. 3-Ethoxycarbonyl—C₆H₄ 194. 4-Ethoxycarbonyl—C₆H₄ 195. 2-CH₂FCH₂—C₆H₄ 196. 3-CH₂FCH₂—C₆H₄ 197. 4-CH₂FCH₂—C₆H₄ 198. 2-CF₃CH₂—C₆H₄ 199. 3-CF₃CH₂—C₆H₄ 200. 4-CF₃CH₂—C₆H₄ 201. 2-CHF₂CF₂—C₆H₄ 202. 3-CHF₂CF₂—C₆H₄ 203. 4-CHF₂CF₂—C₆H₄ 204. 2-CHF₂—C₆H₄ 205. 3-CHF₂—C₆H₄ 206. 4-CHF₂—C₆H₄ 207. 2-NO₂—C₆H₄ 208. 3-NO₂—C₆H₄ 209. 4-NO₂—C₆H₄ 210. 2-CH₃—C₆H₄ 211. 3-CH₃—C₆H₄ 212. 4-CH₃—C₆H₄ 213. 2,3-(CH₃)₂—C₆H₃ 214. 2,4-(CH₃)₂—C₆H₃ 215. 2,5-(CH₃)₂—C₆H₃ 216. 2,6-(CH₃)₂—C₆H₃ 217. 3,4-(CH₃)₂—C₆H₃ 218. 3,5-(CH₃)₂—C₆H₃ 219. 2-C₂H₅—C₆H₄ 220. 3-C₂H₅—C₆H₄ 221. 4-C₂H₅—C₆H₄ 222. 2-i-C₃H₇—C₆H₄ 223. 3-i-C₃H₇—C₆H4 224. 4-i-C₃H₇—C₆H₄ 225. 3-tert.-C₄H₉—C₆H₄ 226. 4-tert.-C₄H₉—C₆H₄ 227. 2-Vinyl—C₆H₄ 228. 3-Vinyl—C₆H₄ 229. 4-Vinyl—C₆H₄ 230. 2-Allyl-C₆H₄ 231. 3-Allyl-C₆H4 232. 4-Allyl-C₆H₄ 233. 2-Propargyl-C₆H₄ 234. 2-Ethinyl-C₆H₄ 235. 3-Propargyloxy-C₆H₄ 236. 4-Butinyloxy-C₆H₄ 237. 2-C₆H₅—C₆H₄ 238. 3-C₆H₅—C₆H₄ 239. 3-CH₃, 5-t-C₄H₉—C₆H₃ 240. 2-F-4-CH₃—C₆H₃ 241. 2-F-5-CH₃—C₆H₃ 242. 2-CH₃-4-F—C₆H₃ 243. 2-CH₃-5-F—C₆H₃ 244. 2-CH₃-4-Cl—C₆H₃ 245. 2-F-4-CH₃—O—C₆H₃ 246. 2-F-4-CH₃CH₂O—C₆H₃ 247. 2-F-4-i-C₃H₇—C₆H₃ 248. 2-Pyridyl 249. 3-Pyridyl 250. 4-Pyridyl 251. 5-CH₃-Pyridin-2-yl 252. 5-Cl-Pyridin-2-yl 253. 6-Cl-Pyridin-2-yl 254. 3,5-Cl₂-Pyridin-2-yl 255. 6-CH₃O-Pyridin-2-yl 256. 6-CH₃-Pyridin-2-yl 257. 6-Cl-Pyridin-3-yl 258. 6-CH₃-Pyridin-3-yl 259. 6-CH₃O-Pyridin-3-yl 260. 2-Pyrimidinyl 261. 4-CH₃O-Pyrimidin-2-yl 262. 4-C₂H₅O-Pyrimidin-2-yl 263. 4-Cl-Pyrimidin-2-yl 264. 4-CH₃-Pyrimidin-2-yl 265. 5-CH₃-Pyrimidin-2-yl 266. 5-Cl-Pyrimidin-2-yl 267. 5-CH₃O-Pyrimidin-2-yl 268. 5-C₂H₅O-Pyrimidin-2-yl 269. 4-Pyrimidinyl 270. 2-Cl-Pyrimidin-4-yl 271. 2-CH₃O-Pyrimidin-4-yl 272. 2-CH₃-Pyrimidin-4-yl 273. 6-Cl-Pyrimidin-4-yl 274. 6-CH₃-Pyrimidin-4-yl 275. 6-CH₃O-Pyrimidin-4-yl 276. 5-Pyrimidinyl 277. 2-CH₃-Pyrimidin-5-yl 278. 2-Cl-Pyrimidin-5-yl 279. 2-CH₃O-Pyrimidin-5-yl 280. 2-C₂H₅O-Pyrimidin-5-yl 281. 2-Furyl 282. 4-C₂H₅-Fur-2-yl 283. 4-CH₃-Fur-2-yl 284. 4-Cl-Fur-2-yl 285. 4-CN-Fur-2-yl 286. 5-CH₃-Fur-2-yl 287. 5-Cl-Fur-2-yl 288. 5-CN-Fur-2-yl 289. 3-Furyl 290. 5-CH₃-Fur-3-yl 291. 5-Cl-Fur-3-yl 292. 5-CN-Fur-3-yl 293. 2-Thienyl 294. 4-CH₃-Thien-2-yl 295. 4-Cl-Thien-2-yl 296. 4-CN-Thien-2-yl 297. 5-CH₃-Thien-2-yl 298. 5-Cl-Thien-2-yl 299. 5-CN-Thien-2-yl 300. 3-Thienyl 301. 5-CH₃-Thien-3-yl 302. 5-Cl-Thien-3-yl 303. 5-CN-Thien-3-yl 304. 2-Oxazolyl 305. 4-CH₃-Oxazol-2-yl 306. 4-Cl-Oxazol-2-yl 307. 4-CN-Oxazol-2-yl 308. 5-CH₃-Oxazol-2-yl 309. 5-Cl-Oxazol-2-yl 310. 5-CN-Oxazol-2-yl 311. 4-Oxazolyl 312. 2-CH₃-Oxazol-4-yl 313. 2-Cl-Oxazol-4-yl 314. 2-CN-Oxazol-4-yl 315. 5-Oxazolyl 316. 2-CH₃-Oxazol-5-yl 317. 2-Cl-Oxazol-5-yl 318. 2-CN-Oxazol-5-yl 319. 3-Isoxazolyl 320. 5-CH₃-Isoxazol-3-yl 321. 5-Cl-Isoxazol-3-yl 322. 5-CN-Isoxazol-3-yl 323. 5-Isoxazolyl 324. 3-CH₃-Isoxazol-5-yl 325. 3-Cl-Isoxazol-5-yl 326. 3-CN-Isoxazol-5-yl 327. 2-Thiazolyl 328. 4-CH₃-Thiazol-2-yl 329. 4-Cl-Thiazol-2-yl 330. 4-CN-Thiazol-2-yl 331. 5-CH₃-Thiazol-2-yl 332. 5-Cl-Thiazol-2-yl 333. 5-CN-Thiazol-2-yl 334. 4-Thiazolyl 335. 2-CH₃-Thiazol-4-yl 336. 2-Cl-Thiazol-4-yl 337. 2-CN-Thiazol-4-yl 338. 2-CH₃S-Thiazol-4-yl 339. 5-Thiazolyl 340. 2-CH₃-Thiazol-5-yl 341. 2-Cl-Thiazol-5-yl 342. 2-CN-Thiazol-5-yl 343. 3-Isothiazolyl 344. 5-CH₃-Isothiazol-3-yl 345. 5-Cl-Isothiazol-3-yl 346. 5-CN-Isothiazol-3-yl 347. 5-Isothiazolyl 348. 3-CH₃-Isothiazol-5-yl 349. 3-Cl-Isothiazol-5-yl 350. 3-CN-Isothiazol-5-yl 351. 2-Imidazolyl 352. 4-CH₃-Imidazol-2-yl 353. 4-Cl-Imidazol-2-yl 354. 4-CN-Imidazol-2-yl 355. 1-CH₃-Imidazol-2-yl 356. 1-CH₃-4-Cl-Imidazol-2-yl 357. 1,4-(CH₃)₂-Imidazol-2-yl 358. 1-CH₃-5-Cl-Imidazol-2-yl 359. 1,5-(CH₃)₂-Imidazol-2-yl 360. 4-Imidazolyl 361. 2-CH₃-Imidazol-4-yl 362. 2-Cl-Imidazol-4-yl 363. 1-CH₃-Imidazol-4-yl 364. 1,2-(CH₃)₂-Imidazol-4-yl 365. 1-CH₃-2-Cl-Imidazol-4-yl 366. 1-CH₃-Imidazol-5-yl 367. 1-CH₃—Cl-Imidazol-5-yl 368. 1,2-(CH₃)₂-Imidazol-5-yl 369. 3-Pyrazolyl 370. 5-CH₃-Pyrazol-3-yl 371. 5-Cl-Pyrazol-3-yl 372. 5-CN-Pyrazol-3-yl 373. 1-CH₃-Pyrazol-3-yl 374. 1-CH₃-4-Cl-Pyrazol-3-yl 375. 1-CH₃-5-Cl-Pyrazol-3-yl 376. 1,5-(CH₃)₂-Pyrazol-3-yl 377. 1-CH₃-Pyrazol-5-yl 378. 1-CH₃-3-Cl-Pyrazol-5-yl 379. 1,3-(CH₃)₂-Pyrazol-5-yl 380. 4-Pyrazolyl 381. 3-Cl-Pyrazol-4-yl 382. 3-CH₃-Pyrazol-4-yl 383. 1-CH₃-Pyrazol-4-yl 384. 1-CH₃-3-Cl-Pyrazol-4-yl 385. 1,3-(CH₃)₂-Pyrazol-4-yl 386. 1,3,4-Oxadiazol-5-yl 387. 2-CH₃-1,3,4-Oxadiazol-5-yl 388. 2-Cl-1,3,4-Oxadiazol-5-yl 389. 2-CF₃-1,3,4-Oxadiazol-5-yl 390. 2-i-C₃H₇-1,3,4-Oxadiazol-5-yl 391. 2-CH₃O-1,3,4-Oxadiazol-5-yl 392. 1,2,4-Oxadiazol-3-yl 393. 5-CH₃-1,2,4-Oxadiazol-3-yl 394. 5-i-C₃H₇-1,2,4-Oxadiazol-3-yl 395. 5-Cl-1,2,4-Oxadiazol-3-yl 396. 5-CF₃-1,2,4-Oxadlazol-3-yl 397. 1,2,4-Triazol-3-yl 398. 1-CH₃-1,2,4-Triazol-3-yl 399. 1-Pyrrolyl 400. 3-CH₃-Pyrrol-1-yl 401. 1-Pyrazolyl 402. 3-CH₃-Pyrazol-1-yl 403. 3-CF₃-Pyrazol-1-yl 404. 4-CH₃-Pyrazol-1-yl 405. 4-Cl-Pyrazol-1-yl 406. 4-Ethoxycarbonyl-Pyrazol-1-yl 407. 3-CH₃-4-Br-Pyrazol-1-yl 408. 1-Imidazolyl 409. 4-CH₃-Imidazol-1-yl 410. 4,5-Cl₂-Imidazol-1-yl 411. 2,4-(CH₃)₂-Imidazol-1-yl 412. 1,2,4-Triazol-1-yl 413. 1,3,4-Triazol-1-yl 414. 3,5-(CH₃)₂-1,2,4-Triazol-1-yl 415. 1-Piperidinyl 416. 1-Pyrrolidinyl 417. 1-Morpholinyl 418. 2-Δ²-Thiazolinyl 419. 5-CH₃-Δ²-Thiazolin-2-yl 420. 5,5-(CH₃)₂-Δ²-Thiazolin-2-yl 421. 4,5-(CH₃)₂-Δ²-Thiazolin-2-yl 422. 2-Δ²-Oxazolinyl 423. 4-CH₃-Δ²-Oxazolin-2-yl 424. 4,4-(CH₃)₂-Δ²-Oxazolin-2-yl 425.

426.

427.

428. Cyclopropoxy 429. Cyclobutoxy 430. Cyclopentoxy 431. Cyclohexyloxy 432. Phenoxy 433. 1-Naphthyloxy 434. 2-Naphthyloxy 435. 2-F—C₆H₄O 436. 3-F—C₆H₄O 437. 4-F—C₆H₄O 438. 2,3-F₂—C₆H₃O 439. 2,4-F₂—C₆H₃O 440. 2,5-F₂—C₆H₃O 441. 2,6-F₂—C₆H₃O 442. 3,4-F₂—C₆H₃O 443. 3,5-F₂—C₆H₃O 444. 2-Cl—C₆H₄O 445. 3-Cl—C₆H₄O 446. 4-Cl—C₆H₄O 447. 2,3-Cl₂—C₆H₃O 448. 2,4-Cl₂—C₆H₃O 449. 2,5-Cl₂—C₆H₃O 450. 2,6-Cl₂—C₆H₃O 451. 3,4-Cl₂—C₆H₃O 452. 3,5-Cl₂—C₆H₃O 453. 2,3,4-Cl₃—C₆H₂O 454. 2,3,5-Cl₃—C₆H₂O 455. 2,3,6-Cl₃—C₆H₂O 456. 2,4,5-Cl₃—C₆H₂O 457. 2,4,6-Cl₃—C₆H₂O 458. 3,4,5-Cl₃—C₆H₂O 459. 2-Br—C₆H₄O 460. 3-Br—C₆H₄O 461. 4-Br—C₆H₄O 462. 2,3-Br₂—C₆H₃O 463. 2,4-Br₂—C₆H₃O 464. 2,5-Br₂—C₆H₃O 465. 2,6-Br₂—C₆H₃O 466. 3,4-Br₂—C₆H₃O 467. 3,5-Br₂—C₆H₃O 468. 2-F-3-Cl—C₆H₃O 469. 2-F-4-Cl—C₆H₃O 470. 2-F-5-Cl—C₆H₃O 471. 2-F-3-Br—C₆H₃O 472. 2-F-4-Br—C₆H₃O 473. 2-F-5-Br—C₆H₃O 474. 2-Cl-3-Br—C₆H₃O 475. 2-Cl-4-Br—C₆H₃O 476. 2-Cl-5-Br—C₆H₃O 477. 3-F-4-Cl—C₆H₃O 478. 3-F-5-Cl—C₆H₃O 479. 3-F-6-Cl—C₆H₃O 480. 3-F-4-Br—C₆H₃O 481. 3-F-5-Br—C₆H₃O 482. 3-F-6-Br—C₆H₃O 483. 3-Cl-4-Br—C₆H₃O 484. 3-Cl-5-Br—C₆H₃O 485. 3-Cl-6-Br—C₆H₃O 486. 4-F-5-Cl—C₆H₃O 487. 4-F-6-Cl—C₆H₃O 488. 4-F-5-Br—C₆H₃O 489. 4-F-6-Br—C₆H₃O 490. 4-Cl-5-Br—C₆H₃O 491. 5-F-6-Cl—C₆H₃O 492. 5-F-6-Br—C₆H₃O 493. 5-Cl-6-Br—C₆H₃O 494. 3-Br-4-Cl-5-Br—C₆H₂O 495. 2-CN—C₆H₄O 496. 3-CN—C₆H₄O 497. 4-CN—C₆H₄O 498. 4-Dimethylaminocarbonyl-C₆H₄O 499. 2-(N-Methylaminocarbonyl)-C₆H₄O 500. 3-(N-Methylaminocarbonyl)-C₆H₄O 501. 4-(N-Methylaminocarbonyl)-C₆H₄O 502. 2-CH₃S—C₆H₄O 503. 3-CH₃S—C₆H₄O 504. 4-CH₃S—C₆H₄O 505. 2-CH₃SO₂—C₆H₄O 506. 3-CH₃SO₂—C₆H₄O 507. 4-CH₃SO₂—C₆H₄O 508. 2-CF₃O—C₆H₄O 509. 3-CF₃O—C₆H₄O 510. 4-CF₃O—C₆H₄O 511. 2-CHF₂O—C₆H₄O 512. 4-CHF₂O—C₆H₄O 513. 4-CHF₂O—C₆H₄O 514. 3-CF₃, 4-CF₃O—C₆H₃O 515. 2-CH₃NH—C₆H₄O 516. 3-CH₃NH—C₆H₄O 517. 4-CH₃NH—C₆H₄O 518. 2-(CH₃)₂N—C₆H₄O 519. 3-(CH₃)₂N—C₆H₄O 520. 4-(CH₃)₂N—C₆H₄O 521. 2-Ethoxycarbonyl-C₆H₄O 522. 3-Ethoxycarbonyl-C₆H₄O 523. 4-Ethoxycarbonyl-C₆H₄O 524. 2-CH₂FCH₂—C₆H₄O 525. 3-CH₂FCH₂—C₆H₄O 526. 4-CH₂FCH₂—C₆H₄O 527. 2-CF₃CH₂—C₆H₄O 528. 3-CF₃CH₂—C₆H₄O 529. 4-CF₃CH₂—C₆H₄O 530. 2-CHF₂CF₂—C₆H₄O 531. 3-CHF₂CF₂—C₆H₄O 532. 4-CHF₂CF₂—C₆H₄O 533. 2-CHF₂—C₆H₄O 534. 3-CHF₂—C₆H₄O 535. 4-CHF₂—C₆H₄O 536. 2-CH₃O—C₆H₄O 537. 3-CH₃O—C₆H₄O 538. 4-CH₃O—C₆H₄O 539. 2,3-(CH₃O)₂—C₆H₃O 540. 2,4-(CH₃O)₂—C₆H₃O 541. 2,5-(CH₃O)₂—C₆H₃O 542. 3,4-(CH₃O)₂—C₆H₃O 543. 3,5-(CH₃O)₂—C₆H₃O 544. 3,4,5-(CH₃O)₃—C₆H₂O 545. 2-C₂H₅O—C₆H₄O 546. 3-C₂H₅O—C₆H₄O 547. 4-C₂H₅O—C₆H₄O 548. 2-(n-C₃H₇O)—C₆H₄O 549. 3-(n-C₃H₇O)—C₆H₄O 550. 4-(n-C₃H₇O)—C₆H₄O 551. 2-(i-C₃H₇O)—C₆H₄O 552. 3-(i-C₃H₇O)—C₆H₄O 553. 4-(i-C₃H₇O)—C₆H₄O 554. 4-(n-C₄H₉O)—C₆H₄O 555. 3-(t-C₄H₉O)—C₆H₄O 556. 4-(t-C₄H₉O)—C₆H₄O 557. 2-Allyl-O—C₆H₄O 558. 3-Allyl-O—C₆H₄O 559. 4-Allyl-O—C₆H₄O 560. 2-CF₃—C₆H₄O 561. 3-CF₃—C₆H₄O 562. 4-CF₃—C₆H₄O 563. 2-Acetyl-C₆H₄O 564. 3-Acetyl-C₆H₄O 565. 4-Acetyl-C₆H₄O 566. 2-Methoxycarbonyl-C₆H₄O 567. 3-Methoxycarbonyl-C₆H₄O 568. 4-Methoxycarbonyl-C₆H₄O 569. 2-Aminocarbonyl-C₆H₄O 570. 3-Aminocarbonyl-C₆H₄O 571. 4-Aminocarbonyl-C₆H₄O 572. 2-Dimethylaminocarbonyl-C₆H₄O 573. 3-Dimethylaminocarbonyl-C₆H₄O 574. 2-NO₂—C₆H₄O 575. 3-NO₂—C₆H₄O 576. 4-NO₂—C₆H₄O 577. 2-CH₃—C₆H₄O 578. 3-CH₃—C₆H₄O 579. 4-CH₃—C₆H₄O 580. 2,3-(CH₃)₂—C₆H₃O 581. 2,4-(CH₃)₂—C₆H₃O 582. 2,5-(CH₃)₂—C₆H₃O 583. 2,6-(CH₃)₂—C₆H₃O 584. 3,4-(CH₃)₂—C₆H₃O 585. 3,5-(CH₃)₂—C₆H₃O 586. 2-C₂H₅—C₆H₃O 587. 3-C₂H₅—C₆H₄O 588. 4-C₂H₅—C₆H₄O 589. 2-i-C₃H₇—C₆H₄O 590. 3-i-C₃H₇—C₆H₄O 591. 4-i-C₃H₇—C₆H₄O 592. 3-t-C₄H₉—C₆H₄O 593. 4-t-C₄H₉—C₆H₄O 594. 2-Vinyl-C₆H₄O 595. 3-Vinyl-C₆H₄O 596. 4-Vinyl-C₆H₄O 597. 2-Allyl-C₆H₄O 598. 3-Allyl-C₆H₄O 599. 4-Allyl-C₆H₄O 600. 2-C₆H₅—C₆H₄O 601. 3-C₆H₅—C₆H₄O 602. 4-C₆H₅—C₆H₄O 603. 3-CH₃-5-t-C₄H₉—C₆H₃O 604. 2-F-4-CH₃—C₆H₃O 605. 2-F-5-CH₃—C₆H₃O 606. 2-CH₃-4-F—C₆H₃O 607. 2-CH₃-5-F—C₆H₃O 608. 2-CH₃-4-Cl—C₆H₃O 609. 2-Pyridyloxy 610. 3-Pyridyloxy 611. 4-Pyridyloxy 612. 2-Pyrimidinyloxy 613. 4-Pyrimidinyloxy 614. 5-Pyrimidinyloxy 615. 1-CH₃-Piperidinyl-3-xy 616. 1-CH₃-Piperidinyl-4-xy

TABLE 61 Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies O and Z corresponds in each case to one line of Table B. I.7

Table 62

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies OCH₂ and Z corresponds in each case to one line of Table B.

Table 63

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies CH₂O and Z corresponds in each case to one line of Table B.

Table 64

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies S and Z corresponds in each case to one line of Table B.

Table 65

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies —C≡C— and Z corresponds in each case to one line of Table B.

Table 66

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies —CH═CH— and Z corresponds in each case to one line of Table B.

Table 67

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies —CH₂—CH₂— and Z corresponds in each case to one line of Table B.

Table 68

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ and R₂ signify methyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.

Table 69

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 70

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies OCH₂ and Z corresponds in each case to one line of Table B.

Table 71

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies CH₂O and Z corresponds in each case to one line of Table B.

Table 72

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies S and Z corresponds in each case to one line of Table B.

Table 73

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies —C≡C— and Z corresponds in each case to one line of Table B.

Table 74

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies —CH═CH— and Z corresponds in each case to one line of Table B.

Table 75

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies —CH₂—CH₂— and Z corresponds in each case to one line of Table B.

Table 76

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies ethyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.

Table 77

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 78

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies OCH₂ and Z corresponds in each case to one line of Table B.

Table 79

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies CH₂O and Z corresponds in each case to one line of Table B.

Table 80

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies S and Z corresponds in each case to one line of Table B.

Table 81

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies —C≡C— and Z corresponds in each case to one line of Table B.

Table 82

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies —CH═CH— and Z corresponds in each case to one line of Table B.

Table 83

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies —CH₂—CH₂— and Z corresponds in each case to one line of Table B.

Table 84

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies methyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.

Table 85

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 86

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies OCH₂ and Z corresponds in each case to one line of Table B.

Table 87

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies CH₂O and Z corresponds in each case to one line of Table B.

Table 88

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies S and Z corresponds in each case to one line of Table B.

Table 89

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies —C≡C— and Z corresponds in each case to one line of Table B.

Table 90

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies —CH═CH— and Z corresponds in each case to one line of Table B.

Table 91

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies —CH₂—CH₂— and Z corresponds in each case to one line of Table B.

Table 92

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.

Table 93

Compounds of the general formula I.7, wherein R₅ signifies methyl, R₁ and R₂ signify methyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 94

Compounds of the general formula I.7, wherein R₅ signifies methyl, R₁ signifies ethyl and R₂ signifies methyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 95

Compounds of the general formula I.7, wherein R₅ signifies methyl, R₁ signifies methyl and R₂ signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 96

Compounds of the general formula I.7, wherein R₅ signifies methyl, R₁ signifies ethyl and R₂ signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 97

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies propargyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 98

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies propargyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 99

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies allyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 100

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies allyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 101

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies n-propyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 102

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies n-propyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 103

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies methyl and R₂ signifies isopropyl, Q signifies O and Z corresponds in each case to one line of Table B.

Table 104

Compounds of the general formula I.7, wherein R₅ signifies H, R₁ signifies ethyl and R₂ signifies isopropyl, Q signifies O and Z corresponds in each case to one line of Table B.

TABLE B No. Z 1. 2-F 2 3-F 3 4-F 4 2-Cl 5 3-Cl 6 4-Cl 7 2-Br 8 3-Br 9 4-Br 10. 2-CH₃ 11. 3-CH₃ 12. 4-CH₃ 13. 2-CH₂CH₃ 14. 3-CH₂CH₃ 15. 4-CH₂CH₃ 16. 4-CH(CH₃)₂ 17. 4-C(CH₃)₃ 18. 2-CF₃ 19. 3-CF₃ 20. 4-CF₃ 21. 2-OCF₃ 22. 3-OCF₃ 23. 4-OCF₃ 24. 4-SCF₃ 25. 4-S(═O)CF₃ 26. 4-S(═O)₂CF₃ 27. 4-CN 28. 2,3-Cl₂ 29. 2,4-Cl₂ 30. 2,5-Cl₂ 31. 2,6-Cl₂ 32. 3,4-Cl₂ 33. 3,5-Cl₂ 34. 3-Cl-4-CF₃ 35. 4-Cl-3-CF₃ 36. 3-F-4-CF₃ 37. 4-F-3-CF₃ 38. 3,4-(—OCH₂—O—) 39. 3,4-(—OCF₂—O—) 40. 3,4-(—OCF₂CF₂—O) 41. 3,5-(CF₃)₂

Details of the physical data in the following Tables: °=m.p. in °Celsius; Number=chemical displacement of R₅ in ¹H-NMR (.δ.in ppm); * isomers

TABLE 105 Compounds of formula I

No. R₁ R₂ R₃ R₅ R₆ R₇ phys. data 105.1 CH₃ CH₃ 4-CH₃—C₆H₄ H CH₃ CH₃ 93° 105.2 CH₃ CH₃ 4-CH₃CH₂—C₆H₄ H CH₃ CH₃ 8.83/ 8.10 * 105.3 CH₃ CH₃ 4-F—C₆H₄ H CH₃ CH₃  88-90° 105.4 CH₃ CH₃ 4-Cl—C₆H₄ H CH₃ CH₃  87-90° 105.5 CH₃ CH₃ 4-Br—C₆H₄ H CH₃ CH₃  97-98° 105.6 CH₃ CH₃ 4-CH₃O—C₆H₄ H CH₃ CH₃  84-87° 105.7 CH₃ CH₃ 4-CH₃CH₂O—C₆H₄ H CH₃ CH₃ 115-117°

TABLE 106 Intermediates of formula II II

No. R₁ R₂ R₃ phys. data 106.1 CH₃ CH₃ 4-CH₃—C₆H₄ 112-114° 106.2 CH₃ CH₃ 4-CH₃CH₂—C₆H₄  92-95° 106.3 CH₃ CH₃ 4-F—C₆H₄ 134-136° 106.4 CH₃ CH₃ 4-Cl—C₆H₄ 118-119° 106.5 CH₃ CH₃ 4-Br—C₆H4 127-129° 106.6 CH₃ CH₃ 4-CH₃O—C₆H₄  87-90° 106.7 CH₃ CH₃ 4-CH₃CH₂O—C₆H₄  92-94°

TABLE 107 Intermediates of formula III III

No. R₅ R₆ R₇ phys. data 107.1 H CH₃ CH₃ 10.13 107.2 H CH₃ CH₃CH₂ 107.3 H CH₃CH₂ CH₃ 107.4 H CH₃CH₂ CH₃CH₂ 107.5 CH₃ CH₃ CH₃ 107.6 CH₃ CH₃ CH₃CH₂ 107.7 CH₃ CH₃CH₂ CH₃ 107.8 CH₃ CH₃CH₂ CH₃CH₂

Formulations may be prepared analogously to those described for example in WO 97/33890.

Biological Examples

In the following patho-systems, compounds from the tables display good activity.

A. Fungicidal Activity

EXAMPLE B-1

Activity Against Puccinia graminis on Wheat

a) Residual Protective Action

6 days after planting, wheat plants are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 percent relative humidity at 20°), the plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated.

b) Systemic Action

5 days after planting, an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.006% active substance, based on soil volume) is poured onto wheat plants. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground. 48 hours later, the plants are infected with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 percent relative humidity at 20°), the plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated.

EXAMPLE B-2

Activity Against Phytophthora infestans on Tomatoes

a) Residual Protective Action

After cultivating for three weeks, tomato plants are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a sporangia suspension of the fungus. Evaluation of the fungal attack takes place 5 days after infection, during which time conditions of 90 to 100 percent relative humidity and a temperature of 20° are maintained.

b) Systemic Action

After cultivating for three weeks, an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.006% active substance, based on soil volume) is poured onto tomato plants. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground. 48 hours later, the plants are infected with a sporangia suspension of the fungus. Evaluation of the fungal attack takes place 5 days after infection, during which time conditions of 90 to 100 percent relative humidity and a temperature of 20° are maintained.

EXAMPLE B-3

Residual Protective Action Against Cercospora arachidicola on Peanuts

Peanut plants of 10 to 15 cm height are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 48 hours later they are infected with a conidia suspension of the fungus. The plants are incubated for 72 hours at 21° and at high atmospheric humidity, and then placed in a greenhouse until the typical leaf spots appear. Evaluation of the activity of the active substance is made 12 days after infection and is based on the number and size of leaf spots.

EXAMPLE B-4

Activity Against Plasmopara viticola on Grapevines

Vine seedlings at the 4 to 5 leaf stage are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a sporangia suspension of the fungus. Evaluation of the fungal attack takes place 6 days after infection, during which time conditions of 95 to 100 percent relative humidity and a temperature of 20° are maintained.

EXAMPLE B-5

Activity Against Colletotrichum lagenarium on Cucumbers

After cultivating for 2 weeks, cucumber plants are sprayed with an aqueous spray mixture prepared from a wettable powder of the active ingredient (concentration 0.002%). After 2 days, the plants are infected with a spore suspension (1.5×10⁵ spores/ml) of the fungus, and incubated for 36 hours at 23° C. and at high humidity. Incubation then continues at normal humidity and at ca. 22° C. The fungal attack that has set in is evaluated 8 days after infection.

EXAMPLE B-6

Residual Protective Action Against Venturia inaequalis on Apples

Apple cuttings with new shoots of 10 to 20 cm length are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a conidia suspension of the fungus. The plants are incubated for 5 days at 90 to 100 percent relative humidity and placed in a greenhouse for a further 10 days at 20 to 24°. 12 days after infection, the fungal attack is evaluated.

EXAMPLE B-7

Activity Against Erysiphe graminis on Barley

a) Residual Protective Action

Barley plants of approximately 8 cm height are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 3 to 4 hours later they are dusted with conidia of the fungus. The infected plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated.

b) Systemic Action

An aqueous spray mixture prepared from a wettable powder of the active ingredient (0.002% active substance, based on soil volume) is poured onto barley plants of approximately 8 cm height. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground. 48 hours later, the plants are dusted with conidia of the fungus. The infected plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated.

EXAMPLE B-8

Activity Against Podosphaera leucotricha on Apple Shoots

Apple cuttings with new shoots of ca. 15 cm length are sprayed with a spray mixture (0.06% active substance). After 24 hours, the treated plants are infected with a conidia suspension of the fungus and placed in a plant-growth chamber at 70% relative humidity and at 20° C. 12 days after infection, the fungal attack is evaluated.

B. Insecticidal Actvity

EXAMPLE B-9

Activity Against Aphis craccivora

Pea seedlings are infected with Aphis craccivora, subsequently sprayed with a spray mixture containing 100 ppm of active ingredient, and then incubated at 20°. The percentage reduction of the population (% response) is determined 3 and 6 days later by comparing the total number of dead aphids on the treated plants with those on the untreated plants.

EXAMPLE B-10

Activity Against Diabrotica balteata

Corn seedlings are sprayed with an aqueous emulsion spray mixture containing 400 ppm of active ingredient, when the spray coating has dried on they are colonised with 10 larvae of the second stage of Diabrotica balteata and then placed in a plastic container. The percentage reduction of the population (% response) is determined 6 days later by comparing the total number of dead larvae on the treated plants with those on the untreated plants.

EXAMPLE B-11

Activity Against Heliothis virescens

Young soya plants are sprayed with an aqueous emulsion spray mixture containing 100 ppm of active ingredient, when the spray coating has dried on they are colonised with 10 caterpillars of the first stage of Heliothis virescens and then placed in a plastic container. The percentage reduction of the population and of the feeding damage (% response) is determined 6 days later by comparing the total number of dead caterpillars and the feeding damage on the treated plants with those on the untreated plants.

EXAMPLE B-12

Activity Against Spodoptera littoralis

Young soya plants are sprayed with an aqueous emulsion spray mixture containing 100 ppm of active ingredient, when the spray coating has dried on they are colonised with 10 caterpillars of the third stage of Spodoptera littoralis and then placed in a plastic container. The percentage reduction of the population and of the feeding damage (% response) is determined 3 days later by comparing the total number of dead caterpillars and the feeding damage on the treated plants with those on the untreated plants.

EXAMPLE B-13

Activity Against Nilaparvata lugens

Rice plants are sprayed with an aqueous emulsion spray mixture containing 100 ppm of active ingredient. After the spray coating has dried on, the rice plants are colonised with plant and leaf-hopper larvae of the second and third stage. 21 days later they are evaluated. The percentage reduction of the population (% response) is determined by comparing the number of surviving plant and leaf-hoppers on the treated plants with those on the untreated plants.

EXAMPLE B-14

Activity Against Plutella xylostella Caterpillars

Young cabbage plants are sprayed with an aqueous emulsion spray mixture containing 100 ppm of active ingredient. After the spray coating has dried on, the cabbage plants are colonised with 10 caterpillars of the third stage of Plutella xylostella and placed in a plastic container. Three days later they are evaluated. The percentage reduction of the population and percentage reduction of feeding damage (% response) are determined by comparing the total number of dead caterpillars and the feeding damage on the treated plants with those on the untreated plants.

EXAMPLE B-15

Activity Against Musca domestica

A sugar cube is treated with a solution of the test compound in such a way that the concentration of test compound in the sugar, after drying over night, is 250 ppm. This treated cube is place on an aluminium dish with wet cottonwool and 10 adult Musca domestica of an OP-resistant strain, covered with a beaker and incubated at 25° C. The mortality rate is determined after 24 hours.

C. Acaricidal Activity

EXAMPLE B-16

Activity Against Tetranychus urticae

Young bean plants are colonised with a mixed population of Tetranychus urticae and, one day later, are sprayed one day later with an aqueous emulsion spray mixture containing 400 ppm of active ingredient. The plants are subsequently incubated for 6 days at 25 ° C. and then evaluated. The percentage reduction of the population (% response) is determined by comparing the total number of dead eggs, larvae, and adults on the treated plants with those on the untreated plants.

EXAMPLE B-17

Activity on Mixed Population of Tetranychus cinnabarinus Dilution Series

Bush beans at the 2-leaf stage are colonised with a mixed population (eggs, larvae/nymphs, adults) of an OP-tolerant strain of Tetranychus cinnabarinus. 24 hours after infection, the products are applied to the plants in an automatic spray canister at dosages of 200, 100, 50 mg AS/I. The substances are ready-formulated and are diluted with water to the appropriate dosages. The test is evaluated 2 and 7 days after application by the percentage mortality of eggs, larvae/nymphs and adults. Compounds of the tables show a mortality of over 70% in dilutions up to 50 mg AS/litre.

EXAMPLE B-18

Activity Against Boophilus microplus

Fully engorged female adult ticks are adhered to a PVC sheet, covered with a wad of cottonwool and then 10 ml of aqueous test solution, containing 125 ppm active ingredient, is poured over them. The cottonwool is removed and the ticks are incubated for 4 weeks to lay eggs. The activity is shown either in the case of females as mortality or sterility or in the case of eggs as ovicidal activity. 

We claim:
 1. A compound of formula I

wherein R₁ is C₁-C₄-alkyl or cyclopropyl; R₂ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl; or C₁-C₆-alkyl substituted by 1 to 5 fluorine atoms; R₃ represents CN, or represents C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₂-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl wherein the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, aminocarbonyl, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, wherein the cyclic radicals in turn may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, optionally substituted benzyl, optionally substituted benzyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl and optionally substituted heteroaryloxy; wherein the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or R₃ represents aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, wherein the above-mentioned groups may be unsubstituted or substituted by one or more identical or different substituents selected from the group comprising halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkyl-sulfonyl, halogen-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-(C₁-C₆-alkyl)-aminocarbonyl, wherein the alkyl groups may be identical or different, C₁-C₆-alkylaminothiocarbonyl, di-(C₁-C₆-alkyl)-aminothiocarbonyl, wherein the alkyl groups may be identical or different, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)-amino, NO₂, an unsubstituted C₁-C₄-alkylenedioxy group or one which is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen; or CN, SF₅, OH and QR₄; Q represents a direct bond, O, O(C₁-C₆-alkylene), (C₁-C₆-alkylene)O, S(═O)p, S(═O)p(C₁-C₆-alkylene), (C₁-C₆-alkylene)S(═O)p, C₁-C₈-alkylene, C₂-C₆-alkenylene or C₂-C₆-alkinylene; R₄ represents an unsubstituted C₂-C₆-alkenyl- or C₂-C₆-alkinyl group or a C₂-C₆-alkenyl- or C₂-C₆-alkinyl group which is substituted by 1 to 3 halogen atoms, or represents a (C₁-C₄-alkyl)₃Si group, wherein the alkyl groups may be identical or different, or represents CN, or represents an unsubstituted or mono- to penta-substituted C₃-C₆-cycloalkyl, aryl, heteroaryl or heterocyclyl group, wherein the substituents are selected from the group comprising halogen, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, phenoxy, CN, SF₅, NO₂, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halogen-C₁-C₆-alkylsulfonyl and C₁-C₄-alkylenedioxy, wherein the alkylenedioxy may be unsubstituted or mono- to tetrasubstituted by C₁-C₄-alkyl and/or by halogen; p is 0, 1 or 2; R₅ represents hydrogen or methyl; and R₆ and R₇ each individually represents C₁-C₄-alkyl.
 2. A compound of formula I according to claim 1, wherein R₁ is methyl or ethyl; R₂ represents methyl, ethyl, fluoromethyl or trifluoroethyl; R₃ represents C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy or C₁-C₆-alkoxycarbonyl, wherein the above-mentioned groups may be partly or wholly halogenated; furthermore CN, OCN or halogen; or phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, wherein the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl; an R₆ and R₇ each independently represent methyl or ethyl.
 3. A compound of formula I according to claim 1, wherein R₁ is methyl or ethyl; R₂ is C₁-C₆-alkyl or C₁-C₆-alkyl substituted by 1 to -5 fluorine atoms; R₃ is CN, or represents unsubstituted, or partly or wholly halogenated C₁-C₆ alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl, or represents an aryl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, wherein the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or represents heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl; and wherein R₆ and R₇ each individually represents methyl or ethyl.
 4. A compound of formula I according to claim 1, in which R₁ is methyl, ethyl or cyclopropyl; R₂ is C₁-C₆ alkyl; R₃ is CN, or represents unsubstituted, or partly or wholly halogenated C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl, or represents an aryl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, wherein the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl; or represents heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl.
 5. A compound of formula I according to claim 1, wherein R₁ represents methyl, ethyl or cyclopropyl; R₂ represents C₁-C₆-alkyl, C₂-C₆-alkenyl, or C₂-C₆-alkinyl, R₃ represents phenyl which may be substituted by one or more identical or different substituents selected from the group comprising halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkyl-sulfonyl, halogen-C₁-C₆-alkylsulfonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl, di-(C₁-C₆-alkyl)-aminocarbonyl, wherein the alkyl groups may be identical or different, C₁-C₆-alkylaminothiocarbonyl, di-(C₁-C₆-alkyl)-aminothiocarbonyl, wherein the alkyl groups may be identical or different, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)-amino, NO₂, an unsubstituted C₁-C₄-alkylenedioxy group or one which is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen; or CN, SF₅, OH and QR₄; Q represents a direct bond, O, O(C₁-C₆-alkylene), (C₁-C₆-alkylene)O, C₁-C₆-alkylene, C₂-C₆-alkenylene or C₂-C₆-alkinylene; R₄ represents an unsubstituted or mono- to penta-substituted C₃-C₆-cycloalkyl, aryl, heteroaryl or heterocyclyl group, wherein the substituents are selected from the group comprising halogen, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, phenoxy, CN, SF₅, NO₂, C₁-C₆-alkylsulfinyl, halogen-C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, halogen-C₁-C₆-alkylsulfonyl and an unsubstituted C₁-C₄-alkylenedioxy or one that is mono- to tetra-substituted by C₁-C₄-alkyl and/or by halogen.
 6. A process for the preparation of a compound of formula I according to claim 1, comprising the step A) reacting a hydrazone of formula II

 wherein R₁, R₂ and R₃ are as defined in claim 1, with an aldehyde or a ketone of formula III or with one of its acetal or imino derivatives of formulae IVa and IVb

 wherein R₅, R₆ and R₇ are as defined in claim 1 and R₈ signifies C₁-C₆-alkyl or the two R₈, together with the two oxygen atoms and the carbon to which they are bonded, represent a cyclic acetal, or B) etherifying a N-hydroxycarbamate of formula V,

wherein R₁—R₃, R₁ and R₆ are defined as for formula I.
 7. A N-hydroxycarbamate of formula V,

wherein R₁—R₃, R₅ and R₆ are defined as for formula I in claim
 1. 8. A N-hydroxyaniline of the formula VI

wherein R₁, R₂, R₃ and R₅ are defined as for formula I in claim
 1. 9. An agrochemical composition comprisingan effective quantity of a compound according to claim 1, and an appropriate carrier.
 10. A process for the control and prevention of plant-pathogenic fungi, acarids and insects comprising the step of applying a compound according to claim 1 to plants or to their locus.
 11. A compound according to claim 2, wherein R₁, R₂, R₆ and R₇ are methyl.
 12. A compound according to claim 3, wherein R₁, R₆ and R₇ are methyl.
 13. A compound according to claim 4, wherein R₁ is methyl and R₂ is methyl or ethyl.
 14. A compound according to claim 5, wherein R₂ is methyl, ethyl, allyl or propargyl.
 15. A compound according to claim 1, wherein R₃ represents CN, OCN or halogen, or represents unsubstituted, partially halogenated or wholly halogenated C₁-C₆-alkyl, unsubstituted, partially halogenated or wholly halogenated C₁-C₆-alkoxy, unsubstituted, partially halogenated or wholly halogenated C₂-C₆-alkenyl, unsubstituted, partially halogenated or wholly halogenated C₂-C₆-alkenyloxy, unsubstituted, partially halogenated or wholly halogenated C₂-C₆-alkinyl, unsubstituted, partially halogenated or wholly halogenated C₃-C₆-alkinyloxy, unsubstituted, partially halogenated or wholly halogenated C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy or unsubstituted, partially halogenated or wholly halogenated C₁-C₆-alkoxycarbonyl.
 16. A compound according to claim 1, wherein R₃ represents phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkinyl, C₃-C₆-alkinyloxy, C₁-C₆-alkoxycarbonyl, CN, OCN, benzyl, phenyl and phenoxy, whereby the benzyl, phenyl and phenoxy may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino and C₂-C₆-alkenyl.
 17. A compound according to claim 1, wherein R₃ represents phenyl which is substituted, preferably in 4-position, by QR₄, wherein Q is a direct bond, O, OCH₂, CH₂O, S, CH₂—CH₂, —CH═CH— or —C≡C—.
 18. A compound according to claim 17, wherein R₄ represents phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, C₂-C₄-alkinyl, C₃-C₄-alkinyloxy, C₁-C₄-alkoxycarbonyl or CN.
 19. A compound according to claim 1, wherein R₃ represents pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, optionally substituted arylcarbonyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, or C₂-C₆-alkenyl.
 20. A compound according to claim 1, wherein R₃ represents phenyl which is substituted in 4-position by QR₄, wherein Q is a direct bond, O, OCH₂, CH₂O, S, CH₂—CH₂, —CH═CH— or —C≡C—, and R₄ represents phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkenyloxy, C₂-C₄-alkinyl, C₃-C₄-alkinyloxy, C₁-C₄-alkoxycarbonyl or CN. 